Watch: Willie Nelson Sing a Medley of His Early, Crooner Hits Circa 1965

The early days of Willie Nelson’s career were a far cry from the music we know and love him for now. Prior to being a tastemaker in the “Outlaw Country” circuit, Nelson was a crooner like many of his fellow Opry country stars. In 1965, Nelson took to the famed revue to perform a selection of his early hits. Check out the moment, below.

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Watch: Willie Nelson Sing a Medley of His Early, Crooner Hits Circa 1965

In 1962, Nelson released ...And Then I Wrote. The album featured a host of Nelson’s early hits, including “Crazy,” “Funny How Time Slips Away,” and “Mr. Record Man.” In his Grand Ole Opry performance, Nelson cycled through the track list of this album.

The album is indicative of how much Nelson struggled to find his footing in Nashville. Even with stellar songs, like the ones he highlighted in this performance, he wasn’t getting the respect his fans likely think he deserved.

“Nashville was a struggle,” he once said of that time in his career. “I moved there in 1960, at about the time I turned 27. I was as broke as the Ten Commandments. As a singer, I had a style, but not everyone liked that style. Nor was I a great guitarist. When I looked at my writing, though, I saw something I genuinely liked. There was no reason I couldn’t compete in the arena where the best writers worked.”

He would later move back to Texas and find a firmer footing in the “Outlaw” movement. Now that we know how successful he would become, its fun to look back to the beginning. In the performance below, Nelson proves why he should’ve been an instant hit with country fans the world over–let alone Nashville.

(Photo by Mike Coppola/WireImage)